The widest selection of unusual accommodations in The Berkshires

A cabin, a lighthouse, a glamping, your extraordinary stay awaits you

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
The Berkshires unique stays
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

344 Unique places to stay in The Berkshires

Best The Berkshires unusual places with a balcony

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires
9.7 132 reviews

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns

cabin, Sandisfield
This charming four-bedroom cottage is situated in Sandisfield, Massachusetts, just 26 kilometres from the Cranwell Spa & Golf Club, 27 kilometres from the Norman Rockwell Museum, and 29 kilometres from Tanglewood, offering easy access to popular attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 184 square metre dwelling comfortably accommodates up to 10 guests and boasts a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy a range of amenities including a tennis court, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Peace And Quiet On The Lake - The Berkshires
9.6 282 reviews

Peace And Quiet On The Lake

apartment, Becket
This charming house is located in Sherwood Forest, just 3.5 kilometres from Pyramid Lake and within 10 kilometres of both Iroquois Waterfront and October Mountain State Forest, offering a peaceful escape from the hustle and bustle. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
This comfortable dwelling features two bedrooms, comfortably accommodating up to six guests. The kitchen is equipped with a refrigerator, oven, stovetop, microwave, and dishwasher, while the private garden provides a relaxing outdoor space with a barbecue grill.

Discover Family-Friendly Unique Stays in The Berkshires

Reconnect with nature during family holidays in The Berkshires staying in accommodation everyone will talk about.

Berkshire Treehouse Retreat - The Berkshires
9.8 158 reviews

Berkshire Treehouse Retreat

cabin, New Marlborough
This double treehouse is located in New Marlborough, just 8km from the town of Great Barrington and a 20-minute drive to its centre. The property has received excellent ratings for location, cleanliness, and overall user experience.
The treehouse has two levels, offering separate sleeping and working spaces, and can accommodate up to five guests. It boasts a unique design, incorporating a live tree running through the interior, and includes a kitchenette, gas grill, solo stove, and outdoor dish station for a comfortable glamping experience.
Berkshires Cedar Cabin: Complete Privacy - The Berkshires
10 10 reviews

Berkshires Cedar Cabin: Complete Privacy

cabin, Otis
This detached lodge is located on four private acres in the Berkshires, offering a secluded woodland setting 4 kilometres from Otis Reservoir and close to hiking, skiing, Jacob's Pillow, and Tanglewood.
This pet-friendly, family-friendly accommodation sleeps six guests across three bedrooms and two bathrooms, featuring a well-stocked kitchen with a fridge, freezer, and microwave, air conditioning on both floors, an electric fireplace, and a sunroom with forest views.
Amazing Berkshire Mountains Cabin - The Berkshires
9.9 308 reviews

Amazing Berkshire Mountains Cabin

cabin, Monterey
This four-bedroom lodge is located just a short drive from the Appalachian Trail, Beartown State Forest, and Lake Garfield, offering a peaceful retreat in the heart of the Berkshire Mountains. It has received excellent ratings for its location, cleanliness, and overall experience.
The 232 square metre property features a fully equipped kitchen, two fireplaces, a hot tub, and a screened porch. Guests can enjoy hiking trails, kayaking, swimming, and access to a fire pit, as well as a selection of DVDs, games, and books.
Berkshires Chalet Natural Setting Deck & Fire Pit! - The Berkshires
9.8 21 reviews

Berkshires Chalet Natural Setting Deck & Fire Pit!

chalet, Otis
This charming chalet is located in the Berkshires, a short drive from Tanglewood and Jacob's Pillow, and a mile from Otis Ridge ski area, offering a peaceful retreat in a beautiful setting. This property has consistently received excellent ratings for its cleanliness, location and overall experience.
The chalet has four bedrooms, three bathrooms, and can comfortably accommodate up to eight guests. It features a spacious living area with a wood-burning stove, a well-equipped kitchen, a large private yard with a fire pit and a screened-in porch, and a variety of amenities for a comfortable stay.

Frequently asked questions about unique stays in The Berkshires

  • What attractions is Monts Berkshire famous for?

    The Berkshires is known for its stunning natural beauty, with the Appalachian Mountains running through the region. You'll find plenty of hiking trails, lakes, and forests to explore. It's also known for its vibrant arts and culture scene, with several world-renowned museums, theaters, and music venues. Tanglewood, the summer home of the Boston Symphony Orchestra, is a must-visit for music lovers.
  • What clothing or gear is recommended for the climate in Monts Berkshire?

    The Berkshires has four distinct seasons, so pack accordingly. In the summer, it's warm and humid, so light clothing is best. In the autumn, it's crisp and cool, so you'll want to pack layers. Winter can be very cold and snowy, so pack warm clothing, a hat, gloves, and a scarf. And don't forget your hiking boots if you plan on exploring the many trails.
  • What are the best ways to travel to Monts Berkshire eco-consciously?

    The Berkshires is easily accessible by train from New York City. The Amtrak train line runs directly to Pittsfield, and from there, you can take a bus or rent a car to get around. Another option is to drive an electric car, as there are several charging stations in the region. If you're flying, consider offsetting your carbon emissions.
  • Which neigbourhood offers the best unique stays in Monts Berkshire?

    Stockbridge is known for its charming inns and bed and breakfasts, many of which are housed in historic buildings. You'll also find several unique accommodations in Lenox, including the historic Cranwell Resort and Spa and the modern The Orchards. For a more rustic experience, head to the Berkshires' western towns, where you can find cabins and glamping sites.
  • What should you know about unique stays in Monts Berkshire before booking?

    Before booking a unique stay, it's important to consider your needs and preferences. Some unique accommodations may be more remote or have limited amenities. It's also important to check the availability and pricing, as these can vary depending on the time of year. Finally, be sure to read reviews from other guests before booking.

Popular destinations

Best Unusual Places to Stay with a Jacuzzi in The Berkshires

Soak in the scenery from a private hot tub at these one-of-a-kind properties-the ultimate way to enjoy a unique stay in The Berkshires.

Amazing Berkshire Mountains Cabin - The Berkshires
9.9 308 reviews

Amazing Berkshire Mountains Cabin

cabin, Monterey
This four-bedroom lodge is located just a short drive from the Appalachian Trail, Beartown State Forest, and Lake Garfield, offering a peaceful retreat in the heart of the Berkshire Mountains. It has received excellent ratings for its location, cleanliness, and overall experience.
The 232 square metre property features a fully equipped kitchen, two fireplaces, a hot tub, and a screened porch. Guests can enjoy hiking trails, kayaking, swimming, and access to a fire pit, as well as a selection of DVDs, games, and books.

Best The Berkshires unusual places with a sauna

Bedroom Forest View I Sauna I Fire-pit I Trails - The Berkshires
9.9 186 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

cabin, New Marlborough
This one-bedroom cabin in New Marlborough is situated beside the Umpachene River, a short distance from the Appalachian Trail and the town centre.
The cabin is equipped with a well-equipped kitchen, a private sauna, and an outdoor shower, comfortably accommodating up to four guests.
Misty Pines Cabin | Wood Stove  Sauna - The Berkshires
10 22 reviews

Misty Pines Cabin | Wood Stove Sauna

cabin, Monterey
This Monterey lodge is located among tall pines, a short distance from Beartown State Forest, Lake Garfield, Steadman Pond, Greene Park, and the Bidwell House Museum.
This three-bedroom, three-bathroom holiday home accommodates eight guests and features a fully equipped kitchen, a wood-fired sauna, a garden, and parking, with a rustic log cabin feel and an outdoor wood-fired sauna for relaxation.

Browse 5-Star Unusual Places to Stay in The Berkshires

Escape to a luxury unique stay in the hills of The Berkshires, where unconventional design meets high-end comfort for a memorable retreat.

Cabin With Spectacular Views Of Robin Hood Lake - The Berkshires
9.5 120 reviews

Cabin With Spectacular Views Of Robin Hood Lake

cabin, Becket

Compare Unusual Places to Stay with a Swimming Pool in The Berkshires

Each mountain unique stay in The Berkshires with a pool provides a revitalising post-hike dip.

Iconic Lodge In The Berkshires - The Berkshires
9.7 63 reviews

Iconic Lodge In The Berkshires

cabin, Sandisfield
©2026 cozycozy.com